The overpriced Pottery Barn monogrammed backpack is hanging on its rightful hook, with matching lunchbox and water bottle clipped into place.

The stressfully obtained school supplies are beautifully packed.

It’s about that time. 

My big boy is officially going off to kindergarten! This makes me want to scream WOOOOO HOOOO!!!!! and cry boo hoo simultaneously.

There are just so many feelings. It’s not all sunshine and unicorns like I swore it would be.

I’ve spent the last four Augusts dreamily gazing at the moms with elementary school kids and their largely open schedules. I love my kids, I do. But the toddler years have been rough for our family with three kids sandwiched into less than 3.5 years.

No matter how I’m feeling, though, the time has come to pack his lunch, comb his hair, and kiss my oldest goodbye for SEVEN hours.

So I’ve made a little list of the woes and woo’s. Maybe you can relate!


  • I don’t have a honey I shrunk the kids machine to shrink down to backpack size and be his little hovering protector. 
  • I have to have him ready by 8:00am. (TERRIFIED.)
  • The big kids might teach him cuss words.
  • Kids might can will be mean.
  • What if he hates it? What if I hate it?
  • What if he misses me and I’m not there?
  • There will be homework. Like actual work we have to do at home. (YIKES.)
  • I have to let go. That’s the bottom line. And it’s hard, y,all. I know you know!


  • I have seven hours with only two kids to care for instead of three. That’s 1/3 less tattling and hair pulling and fighting.
  • I have two mornings every single week that ALL three kids will be in school and I can do everything! It feels legitimately magical. Like a unicorn.
  • My son loves structure and I’m a free spirit. Needless to say, he’s going to love it.
  • I get to make after school snacks like fresh baked chocolate chip cookies. (Or storebought ones.)
  • He gets to eat a hot lunch made by a loving lunch lady! Or a cold lunch, packed with love from mom.
  • He gets to make new friends!
  • He gets to spread those ready wings.

This is happening. And though it won’t be perfect (nothing ever is!) I am breathing deep and trusting that it will be wonderful. That my big boy is in the best of hands with his saintly teacher who has chosen to pour into the future generation for a salary that isn’t nearly enough. I don’t even know the woman but I love her already and my prayers are with her. (25 kindergarteners and one teacher! Girl’s got grit.)

I’m so proud of him. Them. You! All of us crossing a new line this year, whether that’s your first time preschooler, kindergatener, middle schooler (EEEK!), high schooler, or college student.

Cheers to you, mama! And to our incredible little ones who are growing up and changing the world, one beautiful, imperfect day at at time.

What would you add to the woos and woes?!

Olivia is a girl who loves Jesus, is head over heels about her hubby and is beyond thankful for her three miracle babies. Olivia also has lots of children in heaven as a result of recurrent miscarriages. She is passionate about bearing and sharing hope with those walking through the darkness of infertility and miscarriage, and is working on a book entitled "Bearing Hope: Navigating the Darkness of Waiting for a Child." She still can't believe how awesomely God brought Coleton into her family through adoption, and how He blessed them with Annabelle thirteen months later. Baby Calvin was born a couple years later. She teaches yoga, writes, and runs to keep her stress levels under control. On any given day, you might find her singing worship songs in the kitchen, sniffing essential oils, or curled up in the corner crying because mommying is hard. She relies on good friends, holy yoga and yummy food to keep her sane. Read more of her stuff at Liv Ryan.


  1. Aww! Way to go Coleton! And his momma :). This made me both a bit jealous and want to squeeze my sweet baby boy 19-month old a little tighter in these years before he goes off to school! Kids, man, they give you all the emotions don’t they?


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